C-13 NUCLEAR SPIN-SPIN RELAXATION-TIMES (T(2C)S) OF ENANTIOMERS IN THE PRESENCE OF COLUMN PACKING MATERIAL AND SOLVENTS FOR CHIRAL DISCRIMINATION HPLC

To elucidate chiral recognition difference between pairs of enantiomer s which interacted with a cellulosic stationary phase of chiral discri mination high performance liquid chromatography (HPLC), C-13 NMR spect roscopy was applied for enantiomers of 1-phenylethanol, 1-indanol, 1,2 ,3,4,-tetrahydro-1-naphthol, glutethimide, and Troger's base. Their C- 13 nuclear spin-spin relaxation times (T(2C)s) and spectra were obtain ed in deuterated HPLC solvents in the presence of column packing mater ial made of cellulose tris (4-methylbenzoate) coated on silica gel. Th e first-eluted enantiomers on the HPLC showed longer T(2C)s and strong er signal intensities of C-13 NMR spectra than the second-eluted enant iomers. These results indicated that the chiral recognition difference of enantiomers was observed by their T(2C)s and intensities of C-13 N MR spectra. The T-2C difference was found to reflect the retention ord er of enantiomers on the chiral HPLC column. (C) 1996 Wiley-Liss, Inc.